Chemistry 121 Winter 17 Introduction to Organic Chemistry and Biochemistry Instructor Dr. Upali Siriwardane (Ph.D. Ohio State) E-mail: upali@latech.edu Office: 311 Carson Taylor Hall ; Phone: 318-257-4941; Contact me trough e-mail if you have questions Online Tests on Following days December 16, 2016: Test 1 (Chapters 12-13) January 23, 2017 : Test 2 (Chapters 14-16) February 10, 2017 : Test 3 (Chapters 17-19) February 22, 2017 : Test 4 (Chapters 20-22) February 23, 2017: Make Up Exam: Chapters 12-22)

Chapter 19 and GHW#9 Questions and Slides Lipids CHEM 121 Winter 2015

Chapter 19: Lipids 19.1 Structure and Classification of Lipids, 654 19.2 Types of Fatty Acids, 656 19.3 Physical Properties of Fatty Acids, 659 19.4 Energy-Storage Lipids: Triacylglycerols, 661 19.5 Dietary Considerations and Triacylglycerols, 664 19.6 Chemical Reactions of Triacylglycerols, 669 19.7 Membrane Lipids: Phospholipids, 674 19.8 Membrane Lipids: Sphingoglycolipids, 681 19.9 Membrane Lipids: Cholesterol, 682 19.10 Cell Membranes, 684 19.11 Emulsification Lipids: Bile Acids, 687 19.12 Messenger Lipids: Steroid Hormones, 689 19.13 Messenger Lipids: Eicosanoids, 692 19.14 Protective-Coating Lipids: Biological Waxes, 694 19.15 Saponifiable and Nonsaponifiable Lipids, 697 CHEM 121 Winter 2017

Lipids A wide variety of naturally occurring organic compounds classified together on the basis of common solubility properties: insolubility in water insoluble in water CHEM 121 Winter 2017

Lipids A wide variety of naturally occurring organic compounds classified together on the basis of common solubility properties: insolubility in water insoluble in water Lipids include Waxes: Esters of long chain fatty acids and alcohols Triglycerides: Fatty acid esters of glycerol Phospholipids: Fatty acid and phosphate esters of glycerol Prostaglandins: structures based on Eicosanoids Glycolipids: structures based on Spingosine cholesterol, steroid hormones, and bile acids fat-soluble vitamins CHEM 121 Winter 2017

Lipids Waxes: Esters of long chain fatty acids and alcohols CHEM 121 Winter 2017

Lipids Triglycerides: Fatty acid esters of glycerol CHEM 121 Winter 2017

Lipids Phospholipids: Fatty acid and phosphate esters of glycerol CHEM 121 Winter 2017

Lipids Prostaglandins: structures based on Eicosanoids: Immune response to inflammation: Messenger lipids Eicosanoids CHEM 121 Winter 2017

Lipids Glycolipids: structures based on Spingosine Nervous system insulation CHEM 121 Winter 2017

Lipids cholesterol, steroid hormones, and bile acids: Structural and Regulatory CHEM 121 Winter 2017

Lipids Fat-soluble vitamins CHEM 121 Winter 2017

Lipid Structures CHEM 121 Winter 2015

Eicosanoids: Messenger lipids CHEM 121 Winter 2015

Glycolipids based on spingosine CHEM 121 Winter 2015

Lipid classification by function Protective-coating lipids - biological waxes Energy-storage lipids – A fat or oil, triacylglycerols or triglycerides. Membrane lipids - phospholipids, sphingoglycolipids, and cholesterol Emulsification lipids - bile acids, soaps and detergents Chemical messenger lipids – a) Steroid hormones, b) Eicosanoids, and prostaglandins Fat-soluble vitamins – E.g. Vitamin A, D, E and K CHEM 121 Winter 2015

Common Names of Carboxylic Acids

Fatty Acids: Lipid Building Blocks CHEM 121 Winter 2015

Fatty Acid Names CHEM 121 Winter 2015

Fatty Acids: Lipid Building Blocks CHEM 121 Winter 2015

Polyunsaturated fatty acids: omega-3 and omega-6 fatty acids CHEM 121 Winter 2015

Essential Fatty Acids (EFA). Fatty acids that cannot be produced by the body and are necessary for proper metabolism. The OMEGA 6 and OMEGA 3 fatty acids are referred to as Essential Fatty Acids (EFA). CHEM 121 Winter 2015

Physical Properties of Fatty Acids CHEM 121 Winter 2015

1) Give names of the following types of lipids. a) Name:____________ b) Name:____________ c) ) Name:____________ d) Name:____________ CHEM 121 Winter 2015

1) Give names of the following types of lipids. e) Name:____________ f) Name:____________ g) Name:____________ h) Name:____________ CHEM 121 Winter 2015

1) Give names of the following types of lipids. i) Name:____________ j) Name:____________ k) Name:____________ CHEM 121 Winter 2015

2) Give the type, structure notation and names of the following fatty acids. CHEM 121 Winter 2015

following fatty acids: 3) Draw the condensed structures of each of the following fatty acids: a. Decanoic acid b. Stearic acid c. trans-5-Decenoic acid d. cis-5-Decenoic acid CHEM 121 Winter 2015

Esterification of glycerol with three molecules of myristic acid 4) Write an equation for each of the following reactions: Esterification of glycerol with three molecules of myristic acid Base (NaOH) hydrolysis or saponification of glyceryl tristearate CHEM 121 Winter 2015

c) Reaction of decanoic acid with KOH 4) Write an equation for each of the following reactions: c) Reaction of decanoic acid with KOH d) Hydrogenation of linoleic acid CHEM 121 Winter 2015

Phospholipids CHEM 121 Winter 2015

5) What are the structural differences between triglycerides (triacylglycerols) and phospholipids? Where they are found in living organisms? CHEM 121 Winter 2015

Spingosine and Spingolipids CHEM 121 Winter 2015

6) What is a sphingolipid? Draw an example. CHEM 121 Winter 2015

Steroids Contains a characteristic arrangement of four cycloalkane rings that are joined to each other. Examples of steroids include the dietary fat cholesterol: CHEM 121 Winter 2015

7) What is a steroid? What are their applications? CHEM 121 Winter 2015

8) What are the two major types of fat substitutes and how they work CHEM 121 Winter 2015

How aspirin relieves pain and inflammation? Aspirin inhibits the production of prostaglandins Concept of COX enzyme inhibition CHEM 121 Winter 2015

Acetaminophen (Tylanol) CHEM 121 Winter 2015

Triglycerides and lipoproteins: high-density (HDL)or (LDL) lipoproteins Lipoprotein particles: chylomicrons Triglycerides transportation in the blood stream CHEM 121 Winter 2015

Four major groups of plasma lipoproteins. 1. Chylomicrons 2. Very low-density lipoproteins (VLDL) 3. Low-density lipoproteins (LDL) 4. High-density lipoproteins (HDL) CHEM 121 Winter 2015

Triglycerides and lipoproteins: high-density (HDL)or (LDL) lipoproteins Lipoprotein particles: chylomicrons Triglycerides transportation in the blood stream chylomicron remnant CHEM 121 Winter 2015

The roles of HDL, LDL, and cholesterol. Cholesterol and lipoproteins are related plaque that causes heart attacks and most strokes. When LDL levels are low, atherosclerosis and heart attacks are almost unknown. High HDL levels are associated with a reduced risk of heart disease: "good" cholesterol CHEM 121 Winter 2015